Dr. Martens - Do or Don't?

I've been thinking since around mid last year I should get some Dr. Martens boots. I have tarsal coalition (as you have read about here before) where two of the bones in each of my ankles are partially fused, causing pain and swelling when on my feet for long periods. Problem is, my job basically demands be to be on my feet for long periods, so I find runners and boots to be most supportive. My work environment is pretty casual - we can get away with jeans and runners if we want, but I'll usually wear jeans or leggings and boots with a casual top or cardigan. Last year I tried on a pair of Dr. Martens 1460 boots in a shop in DFO Moorabbin, and, looking down at my feet, thought they looked very much like school shoes and also that I looked like I was wearing men's boots. However I really should have tried them with skinny jeans or leggings to get the proper effect. Now that we're slowly on the way to winter, I'm wondering if I should invest in a pair and begin breaking them in in time for Winter:

I love the patent black, but wondering if it is a bit too 90s grunge? Yesterday I saw a girl wearing these around Chadstone and they looked soooooo good.

Regular black would be most versatile, however the current ones come with a giant Dr. Martens logo imprinted on the top outside of each boot, which I'm not so keen on. These were the ones I tried on and felt looked like men's work boots. Incidentally, I saw a girl at the hairdressers yesterday wearing these - two Docs sightings in one day. These things are definitely making a comeback. 

Then there is cherry red. Cherry red looks so good but it's not as practical as black. However may look a little more girly?

Did you have Dr. Martens back in the day? I never had any but I really wanted the 3 hole school shoes, however my school was super strict and did not allow yellow stitching on shoes, effectively banning Docs school shoes at school. Also, I don't think my mum would have forked out the cash for them. These boots remind me of the 90s though, just the look and the popularity and also those yellow Dr. Martens boots Zac Hanson had. I miss the 90s! Do you think they are a do or don't for a casual work environment? If you have them, have you purchased them recently or have you dragged out your old boots from the 90s (or earlier)? If you have them, how would you rate them for comfort and support? Most importantly, should I get some?!